IVAS 2022 banner
IVES 9 IVES Conference Series 9 IVAS 9 IVAS 2022 9 Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Abstract

(+)-Catechin—laccase oxidation dimeric standards were hemi-synthesized using laccase from Trametes versicolor in a water-ethanol solution at pH 3.6. Eight fractions corresponding to eight potential oxidation dimeric products were detected. The fractions profiles were compared with profiles obtained with two other oxidoreductases: polyphenoloxidase extracted from grapes and laccase from Botrytis cinerea. The profiles were very similar, although some minor differences suggested possible dissimilarities in the reactivity of these enzymes. Five fractions were then isolated and analyzed by 1D and 2D NMR spectroscopy. The addition of traces of cadmium nitrate in the samples solubilized in acetone-d6 led to fully resolved NMR signals of phenolic protons, allowing the unambiguous structural determination of six reaction products, one of the fractions containing two enantiomers. These products were then analyzed in grape seed extracts and red wines (UHPLC-Q-Orbitrap MS). The different dimers had different fragmentation patterns according to their interflavan linkage position. Oxidation dimeric compounds had a specific fragment ion at m/z 393, missing for B-Type dimers fragmentations. A fragment ion at m/z 291 occurred and was specific for oxidation dimeric compounds with a C-O-C linkage. Higher level oxidation products had abundant specific fragments: m/z 425, 397 and 245. These fragmentations were useful to identify them in complex samples such as grape seed extracts and wines. Three grape varieties and three ripening stages were selected and the corresponding seed extracts were obtained. The analyses revealed an increasing trend for the oxidation markers during grape ripening. The analysis of Syrah wines (2018, 2014, 2010) showed a decreasing trend of these molecules during wine ageing which might be due to further oxidation.

DOI:

Publication date: June 23, 2022

Issue: IVAS 2022

Type: Article

Authors

Saucier Cedric1, Deshaies Stacy1, Le Guernevé Christine1,2, Sommerer Nicolas1,2, Garcia Lucas Suc François1, Mouls Laetitia1

1SPO, Université de Montpellier, INRAE, Institut Agro, UMR SPO, Faculté de Pharmacie, 15 avenue Charles Flahault, 34000 Montpellier, France
2INRAE, PROBE Research Infrastructure, PFP Polyphenol Facility, 34060 Montpellier, France

Contact the author

Keywords

wine, grape, polyphenol,oxidation, catechin

Tags

IVAS 2022 | IVES Conference Series

Citation

Related articles…

Cinétique de développement de la Pourriture Noble dans différents terroirs des Coteaux du Layon : mise au point d’une méthodologie

Dans la région des Coteaux du Layon, en Maine et Loire, l’effet terroir et son déterminisme sont étudiés dans le cadre de la production des vins liquoreux.
Ces vins sont le résultat d’une maturité poussée au delà de celle prévue par la nature afin de donner aux baies une teneur en sucre et en matière sèche très forte, pour mieux valoriser ces effets de la surmaturation, les baies sont récoltées selon la méthode des tries successives (Asselin et al, 1996). Ainsi, on ne récolte à chaque passage que les grains ayant atteint le niveau de concentration requis pour obtenir des vins à fort degré d’alcool avec des sucres résiduels.

Read More

Phenolic extraction during fermentation as affected by ripeness level of Syrah/R99 grapes

L’extraction phénolique au cours de la fermentation à partir de vendanges de différents degrees de maturité du cépage Syrah/R99 a été etudiée. Cette travail fait parti d’un projet focalisé sur la qualité du raisin et des vins obtenus au cours du millésime 2002. Les vignes sont situées à Stellenbosch (Afrique du Sud) sur un sol Glenrose

Read More

Effect of stilbenes on malolactic fermentation performance of onoccocus oeni and lactiplantibacillus plantarum strains in wine production

Malolactic fermentation (MLF) is an important step in winemaking to improve wine quality through deacidification, increased microbial stability, and altered wine flavor. The phenolic composition of wine influences the growth and metabolism of lactic acid bacteria (lab) used for MLF.

Read More

ASSESSING THE ROLE OF 27 KNOWN BITTER COMPOUNDS IN COMMERCIAL WHITE WINES COMBINING LC-MS QUANTIFICATION AND SENSORY ANALYSIS

The balance between the different flavours of a wine largely determines its perception and appreciation by the consumers. In white wines, sweetness and sourness are usually the two poles balancing the taste properties. The bitter flavour, on the other hand, is frequently associated with a loss of equilibrium and all white wines (dry and sweet, young and aged) are affected.
Several bitter compounds are already well-described in wines.

Read More

Influence des facteurs naturels du terroir sur la maturation du raisin en Alsace

A study of the influence of environmental factors on the ripening of grapes under the conditions of Alsace is carried out. Emphasis is placed on the analysis of the mesoclimate and pedoclimate. The experiment is conducted on a network of plots of gewurztraminer grafted on SO4. The production conditions are standardized throughout the device.

Read More